Initially a canon (Domherr), from 1565 he became cathedral dean (Domdechant) of Cologne under Archbishops Frederick IV of Wied and Salentin of Isenburg.
Soon afterwards, in February 1574, Henry married Jutta of Mallinkrodt, a former nun whom he had already met when he was the dean of Cologne Cathedral at the monastery of St. Querinus in Neuss.
Two sons (Wilhelm and Karl I Sayn) emerged from this relationship and although they retained the right to use old family crest (the white castle on the black shield), they were not entitled to inherit because of their illegitimate descent.
As he was becoming increasingly frail, Henry handed over the rule of the county on 12 September 1605 to the husband of his niece, who henceforth called himself William III, Count of Sayn-Wittgenstein-Sayn, believing he had guaranteed the survival of the Lutheran denomination in Sayn.
One of his positive legacies was that he gave Freusburg Castle its present appearance; he was the architect of the south wing with its oriel borne on fabulous stone animals.